EP0403618B2 - Esters methyliques aldimino- ou cetimino-oxy-ortho-tolylacryliques, mode de fabrication et fongicides contenant a ces composes - Google Patents

Esters methyliques aldimino- ou cetimino-oxy-ortho-tolylacryliques, mode de fabrication et fongicides contenant a ces composes Download PDF

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Publication number
EP0403618B2
EP0403618B2 EP89913190A EP89913190A EP0403618B2 EP 0403618 B2 EP0403618 B2 EP 0403618B2 EP 89913190 A EP89913190 A EP 89913190A EP 89913190 A EP89913190 A EP 89913190A EP 0403618 B2 EP0403618 B2 EP 0403618B2
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EP
European Patent Office
Prior art keywords
methyl
chlorophenyl
ethyl
tolyl
cyclopropyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
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EP89913190A
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German (de)
English (en)
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EP0403618A1 (fr
EP0403618B1 (fr
Inventor
Hans Peter Isenring
Stephan Trah
Bettina Weiss
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Bayer AG
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Bayer AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/335—Radicals substituted by nitrogen atoms not forming part of a nitro radical
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    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
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    • A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
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    • A01N43/26—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
    • A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
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    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D277/28—Radicals substituted by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/14—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C07D307/81—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/58—Radicals substituted by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/28—Halogen atoms

Definitions

  • the present invention relates to substituted 2-phenyl-3-methoxyacrylic acid methyl esters of the general formula in which R 1 and R 2 have the following meanings: R 1 R 2 3,5-di (trifluoromethyl) phenyl methyl 2-fluoro-5-methylphenyl methyl 2-benzofuranyl methyl 2-quinolinyl hydrogen 4-fluorophenyl methyl 4-nitrophenyl methyl 4-chlorophenyl methyl 4-chlorophenyl Ethyl ⁇ -Phenylvesthenyl methyl o-tolyl methyl p-anisyl methyl 4-biphenylyl methyl cyclopropyl cyclopropyl ⁇ - (2-furyl) -questionedhenyl methyl ⁇ - (3,4,5-trimethoxy-phenyl) -relihenyl methyl ⁇ , ⁇ , ⁇ , -trifluoro-m-tolyl methyl 3-Bromophenyl methyl 2-chlorophen
  • the compounds according to the invention have fungicidal properties and are suitable as fungicidal active substances, in particular for use in agriculture and horticulture.
  • the invention further relates to a process for the preparation of the compounds according to the invention, fungicidal compositions which contain such compounds as active ingredients, and the use of such compounds and compositions for controlling fungi in agriculture and horticulture.
  • This reaction is a nucleophilic substitution which can be carried out under the reaction conditions customary in this regard.
  • the leaving group U present in the benzyl alcohol derivative of the formula (III) is preferably to be understood as meaning chlorine, bromine, iodine, mesyloxy or tosyloxy.
  • the reaction is conveniently carried out in an inert organic diluent such as a cyclic ether, e.g. Tetrahydrofuran or dioxane, acetone, dimethylformamide or dimethyl sulfoxide, in the presence of a base such as sodium hydride, sodium or potassium carbonate, a tertiary amine, e.g.
  • a trialkylamine especially diazabicyclononane or diazabicycloundecane, or silver oxide, at temperatures between -20 ° C and 80 ° C, preferably in the temperature range from 0 ° C to 20 ° C.
  • reaction can be carried out with phase transfer catalysis in an organic solvent such as methylene chloride in the presence of an aqueous basic solution, e.g. Sodium hydroxide solution, and a phase transfer catalyst, such as tetrabutylammonium hydrogen sulfate, take place at room temperature.
  • organic solvent such as methylene chloride
  • a phase transfer catalyst such as tetrabutylammonium hydrogen sulfate
  • the compounds of the formula I 'thus prepared can be isolated and purified by methods known per se. Any isomer mixtures obtained, e.g. E / Z isomer mixtures into which pure isomers are separated, for example by chromatography or fractional crystallization.
  • the starting materials of formula (III) can also be prepared in a manner known per se, e.g. as described in European Patent Publication No. 203,606 (BASF) and in the literature cited therein.
  • the compounds according to the invention have a fungicidal action and can accordingly be used for combating fungi in agriculture, horticulture and in wood processing. They are particularly suitable for inhibiting the growth or for destroying phytopathogenic fungi on parts of plants, e.g. Leaves, stems, roots, tubers, fruits or flowers, and on seeds and on harmful fungi that occur in the soil. Furthermore, wood-degrading and wood-staining fungi can be combated with the compounds according to the invention.
  • the compounds according to the invention are, for example, active in combating fungi of the classes Deuteromycetes, Ascomycetes, Basidiomycetes and Phycomycetes.
  • the compounds furthermore act, for example, against fungi of the genera Tilletia, Ustilago, Rhizotonia, Verticillium, Fusarium, Pythium, Gaeumannomyces, Sclerotinia, Monilia, Botrytis, Peronospora, Bremia, Gloeosporium, Cercosporidium, Penicillium, Ceratocystis, Rhynophephosphorium, Rhynophephosphorium, Rhynophephosphorium, Rhynophephosphorium, Rhynophephosphorium, Rhynophephosphorium, Rhynophephosphorium, Rhynophephosphorium, Rhynophephosphorium, Rhynophephosphorus, Rhynophephosphorus, Rhynophephosphorus, Rhynophephosphorus, Rhynophephosphorus, Rhynophephosphorus, Rhynophephosphorus, Rhynophephosphorus, Rhynophephosphorus, Rhynophephosphorus, Rh
  • the compounds according to the invention are distinguished by a prophylactic and curative action.
  • the compounds according to the invention act against phytopathogenic fungi under greenhouse conditions even at concentrations of 0.5 mg to 500 mg of active ingredient per liter of spray mixture.
  • doses of 20 g to 1 kg of active ingredient of the formula I 'per hectare and treatment are advantageously used.
  • the following are essentially suitable as solid carriers: natural minerals, such as kaolin, clays, kieselguhr, talc, bentonite, chalk, e.g. Sludge chalk, magnesium carbonate, limestone, quartz, dolomite, attapulgite, montmorillonite and diatomaceous earth; synthetic minerals such as finely divided silica, aluminum oxide and silicates: organic substances such as cellulose, starch, urea and synthetic resins; and fertilizers such as phosphates and nitrates, such carriers e.g. can be present as granules or powder.
  • natural minerals such as kaolin, clays, kieselguhr, talc, bentonite, chalk, e.g. Sludge chalk, magnesium carbonate, limestone, quartz, dolomite, attapulgite, montmorillonite and diatomaceous earth
  • synthetic minerals such as finely divided silica, aluminum oxide and silicates: organic substances such as cellulose, starch, urea
  • solvents or dispersing agents aromatics, such as toluene, xylenes, benzene and alkylnaphthalenes; chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes and methylene chloride; aliphatic hydrocarbons, such as cyclohexane and paraffins, for example petroleum fractions; Alcohols, such as butanol and glycol, and their ethers and esters; Ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone; and strongly polar solvents or dispersing agents, such as dimethylformamide, N-methylpyrrolidone and dimetyhyl sulfoxide, such solvents or dispersing agents preferably having flash points of at least 30 ° C.
  • aromatics such as toluene, xylenes, benzene and alkylnaphthalen
  • liquefied gaseous extenders or carriers which are products which are at room temperature, are also suitable among the solvents or dispersants and are gaseous under normal pressure.
  • examples of such products are, in particular, aerosol propellants, such as halogenated hydrocarbons, for example dichlorodifluoromethane.
  • aerosol propellants such as halogenated hydrocarbons, for example dichlorodifluoromethane.
  • organic solvents can, for example, also be used as auxiliary solvents.
  • the surfactants can be nonionic compounds, such as condensation products of fatty acids, fatty alcohols or fat-substituted phenols with ethylene oxide, fatty acid esters and ethers of sugars or polyhydric alcohols; the products obtained from sugars or polyhydric alcohols by condensation with ethylene oxide; Block polymers of ethylene oxide and propylene oxide; or alkyldimethylamine oxides.
  • the surfactants can also be anionic compounds, such as soaps; Fatty sulfate esters, e.g. Dodecyl sodium sulfate, octadecyl sodium sulfate and cetyl sodium sulfate; Alkyl sulfonates, aryl sulfonates and fatty aromatic sulfonates such as alkyl benzene sulfonates, e.g. Calcium dodecylbenzenesulfonate; and butylnaphthalenesulfonates; and more complex fatty sulfonates, e.g. the amide condensation products of oleic acid and N-methyl taurine and the sodium sulfonate of dioctyl succinate.
  • Fatty sulfate esters e.g. Dodecyl sodium sulfate, octadecyl sodium sulfate and cetyl sodium sulf
  • the surfactants can be cationic compounds, such as alkyldimethylbenzylammonium chlorides, dialkyldimethylammonium chlorides, alkyltrimethylammonium chlorides and ethoxylated quaternary ammonium chlorides.
  • lignin sodium and ammonium salts of lignin sulfonic acid, sodium salts of maleic anhydride-diisobutylene copolymers, sodium and ammonium salts of sulfonated polycondensation products made from naphthalene and formaldehyde and sulfite waste liquors.
  • dispersants which are particularly suitable as thickening or anti-settling agents, e.g. Methyl cellulose, carboxymethyl cellulose, hydroxyethyl cellulose, polyvinyl alcohol, alginates, caseinates and blood albumin can be used.
  • Suitable stabilizers are acid-binding agents, e.g. Epichlorohydrin, phenylglycidyl ether and soya epoxides, antioxidants, e.g. Gallic acid esters and butylated hydroxytoluene; UV absorbers, e.g. substituted benzophenones, diphenylacrylonitrile acid esters and cinnamic acid esters; and deskativators, e.g. Salts of ethylenediaminetetraacetic acid and polyglycols.
  • acid-binding agents e.g. Epichlorohydrin, phenylglycidyl ether and soya epoxides
  • antioxidants e.g. Gallic acid esters and butylated hydroxytoluene
  • UV absorbers e.g. substituted benzophenones, diphenylacrylonitrile acid esters and cinnamic acid esters
  • deskativators e
  • the fungicidal compositions according to the invention can also contain other active compounds, e.g. other fungicides, insecticides and acaricides, bactericides, plant growth regulators and fertilizers.
  • active compounds e.g. other fungicides, insecticides and acaricides, bactericides, plant growth regulators and fertilizers.
  • Such combination agents are suitable for spreading the spectrum of activity or for specifically influencing plant growth.
  • the fungicidal compositions according to the invention contain between 0.0001 and 85 percent by weight of compounds according to the invention as active ingredient (s). They can be in a form suitable for storage and transportation. In such forms, for example emulsifiable concentrates, the active ingredient concentration is normally in the higher range of the above concentration interval. These forms can then be diluted with the same or different formulation adjuvants to active ingredient concentrations that are suitable for practical use, and such concentrations are normally in the low range of the above concentration interval.
  • Emulsifiable concentrates generally contain 5 to 85 percent by weight, preferably 25 to 75 percent by weight, of the compound (s) according to the invention.
  • Ready-to-use solutions, emulsions and suspensions which are suitable, for example, as spray liquors, are suitable as use forms.
  • spray liquors for example, concentrations between 0.0001 and 20 percent by weight available.
  • spray liquors can be formulated in which the active compound concentration is preferably from 0.5 to 20 percent by weight, while the spray liquors formulated in the low-volume process and in the high-volume process preferably have an active compound concentration of 0. 02 to 1.0 or 0.002 to 0.1 percent by weight.
  • the fungicidal compositions according to the invention can be prepared by mixing at least one compound according to the invention with formulation auxiliaries.
  • the preparation of the agents can be carried out in a known manner, e.g. by mixing the active ingredient with solid carriers, by dissolving or suspending in suitable solvents or dispersing agents, possibly using surfactants as wetting agents or emulsifiers or dispersing agents, by diluting previously prepared emulsifiable concentrates with solvents or dispersing agents, etc.
  • the active ingredient can be mixed with a solid carrier, e.g. by grinding together; or you can impregnate the solid carrier with a solution or suspension of the active ingredient and then remove the solvent or dispersant by evaporation, heating or by suction under reduced pressure.
  • a solid carrier e.g. by grinding together; or you can impregnate the solid carrier with a solution or suspension of the active ingredient and then remove the solvent or dispersant by evaporation, heating or by suction under reduced pressure.
  • surfactants or dispersing agents such powdery agents can be made easily wettable with water, so that they can be dissolved in aqueous suspensions, e.g. suitable as a spray, can be transferred.
  • the compounds of the invention can also be mixed with a surfactant and a solid carrier to form a wettable powder which is dispersible in water, or they can be mixed with a solid pre-granulated carrier to form a granular product.
  • a compound according to the invention can be dissolved in a water-immiscible solvent, such as, for example, an alicyclic ketone, which advantageously contains dissolved emulsifier, so that the solution has a self-emulsifying effect when added to water.
  • a water-immiscible solvent such as, for example, an alicyclic ketone, which advantageously contains dissolved emulsifier, so that the solution has a self-emulsifying effect when added to water.
  • the active ingredient can be mixed with an emulsifier and the mixture can then be diluted with water to the desired concentration.
  • the active ingredient can be dissolved in a solvent and then mixed with an emulsifier.
  • Such a mixture can also be diluted with water to the desired concentration. In this way, emulsifiable concentrates or ready-to-use emulsions are contained.
  • the agents according to the invention can be used according to the application methods customary in crop protection or in agriculture.
  • the method according to the invention for combating fungi is characterized in that the goods to be protected, e.g. Plants, parts of plants or seeds, treated with an effective amount of a compound or agent according to the invention.
  • An emulsifiable concentrate has the following composition: g / liter Active ingredient (compound according to the invention) 100 Nonylphenol (10) ethoxylate (non-ionic emulsifier) 50 Calcium dodecylbenzenesulfonate (anionic emulsifier) 25 N-methyl-2-pyrrolidone (solubilizer) 200 Mixture of alkylbenzenes (solvents) ad 1 l
  • the active ingredient and the emulsifiers are dissolved in the solvent and in the solubilizer.
  • a ready-to-use spray mixture of any concentration can be prepared by emulsifying this concentrate in water.
  • a pointed powder has the following composition: Wt .-% Active ingredient (compound according to the invention) 25.0 Silica (hydrated: carrier) 20.0 Sodium lauryl sulfate (wetting agent) 2.0 Sodium lignosulfonate (dispersant) 4.0 Kaolin (carrier) 49.0
  • the components are mixed together and the whole is finely ground in a suitable mill. Dispersing the mixture in water results in a suspension that is suitable as a ready-to-use spray mixture.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Environmental Sciences (AREA)
  • Plant Pathology (AREA)
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  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Zoology (AREA)
  • Pest Control & Pesticides (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pyridine Compounds (AREA)
  • Escalators And Moving Walkways (AREA)
  • Saccharide Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Claims (5)

  1. Composés de formule générale    dans laquelle R1 et R2 ont la signification suivante : R1 R2 3,5-di-(trifluorométhyl)-phényle Méthyle 2-fluoro-5-méthylphényle Méthyle 2-benzofurannyle Méthyle 2-quinoléinyle Hydrogène 4-fluorophényle Méthyle 4-nitrophényle Méthyle 4-chlorophényle Méthyle 4-chlorophényle Ethyle β-phényléthényle Méthyle o-tolyle Méthyle p-anisyle Méthyle 4-biphénylyle Méthyle Cyclopropyle Cyclopropyle β-(2-furyl)-éthényle Méthyle β-(3,4,5-triméthoxyphényl)-éthényle Méthyle α, α, α-trifluoro-m-tolyle Méthyle 3-bromophényle Méthyle 2-chlorophényle Méthyle 3-nitrophényle Méthyle 5-chloro-3-méthyl-2-benzothiényle Méthyle 3-chlorophényle Méthyle 3,4-dichlorophényle Méthyle 2,4-dichlorophényle Méthyle 2,4-dichlorophényle 3-pyridylméthyle 3-méthyl-2-benzothiényle Méthyle 2,5-dichlorophényle Méthyle 4-éthylphényle Méthyle 3-éthylphényle Méthyle 3,4-diméthylphényle Méthyle 6-méthyl-2-naphtyle Méthyle 4-difluorométhoxyphényle Méthyle 4-chlorophényle Néopentyle 3,5-di-(trifluorométhyl)-phényle Ethyle 3-phénantryle Méthyle 2-fluorényle Méthyle Isopropyle Méthyle 4-chlorophényle n-propyle 4-chlorophényle Cyclopropyle 3-chlorophényle Ethyle 4-fluorophényle Ethyle 4-bromophényle Ethyle 4-tert-butylphényle Méthyle Cyclopropyle Méthyle 2-quinoléinylméthyle Méthyle 3-fluoro-5-trifluorométhylphényle Méthyle 3,5-difluorophényle Méthyle 3,5-difluorophényle Ethyle 2-fluoroohényle Ethyle 3,4-diméthoxyphényle Méthyle p-tolyle Ethyle 3-trifluorométhoxyphényle Méthyle 3-fluoro-5-trifluorométhylphényle Ethyle Cyclohexyle Méthyle 4-chlorophényle Trifluorométhyle 3,4-diméthoxybenzyle Méthyle α, α, α-trifluoro-m-tolyle Trifluorométhyle α, α, α-trifluoro-m-tolyle Ethyle 3,5-dichlorophényle Méthyle β-(2-naphtyl)éthényle Trifluorométhyle Méthyle Méthyle α, α, α-trifluoro-m-tolyle n-propyle α, α, α-trifluoro-m-tolyle Cyclopropyle 2-chloro-5-trifluorométhylphényle Méthyle 2-méthylthio-5-trifluorométhylphényle Méthyle 4-chloro-3-trifluorométhylbenzyle Méthyle 4-méthoxybenzyle Méthyle α, α, α-trifluoro-m-tolyle Isopropyle α, α, α-trifluoro-m-tolyle α, α, α-trifluoro-m-tolyle 4-éthoxyphényle Méthyle 3-chloro-4-fluorophényle Méthyle 2,3-dichlorophényle Méthyle p-tolyle Trifluorométhyle 4-(2,4-dichlorophénoxy)-phényle Méthyle 4-(4-nitrophénoxy)-phényle Méthyle 4-(4-méthoxyphénoxy)-phényle Méthyle 3,4-méthylènedioxyphényle Méthyle 7-benzodioxannyle Méthyle 3-bromophényle Ethyle 3-fluoro-5-trifluorométhylphényle Cyclopropyle 2,3,4-trichlorophényle Méthyle 4-chloro-3-méthylphényle Méthyle p-tolyle n-propyle 4-phénoxyphényle Cyclopropyle 3-bromophényle Cyclopropyle 3-chlorophényle Cyclopropyle 3-fluorophényle Cyclopropyle 3-bromophényle n-propyle 3-chlorophényle n-propyle 4-fluoro-3-trifluorométhylphényle n-propyle 3-fluorophényle n-propyle 4-phénoxyphényle n-propyle 3-fluoro-5-trifluorométhylphényle n-propyle 3-bromophényle Trifluorométhyle 3-chlorophényle Trifluorométhyle 4-phénoxyphényle Trifluorométhyle 3-bromophényle Isopropyle 3-chlorophényle Isopropyle 4-phénoxyphényle Isopropyle 4-fluoro-3-trifluorométhylphényle Cyclopropyle 4-fluorophényle Cyclopropyle 4-(n-propyl)-phényle Méthyle 4-méthoxy-3-nitrophényle Méthyle 2,4-diméthoxyphényle Méthyle 4-fluoro-3-trifluorométhylphényle Isopropyle 3-iodophényle Méthyle 4-iodophényle Méthyle 2-(4-méthoxyphényl)-éthyle Méthyle 1,4,8-triméthyl-nona-1,3,7-triényle Méthyle 1-méthyl-2-(3,4-méthylènedioxyphényl)-éthyle Méthyle
  2. Produit fongicide, caractérisé en ce qu' il contient une quantité efficace d'au moins un composé selon la revendication 1 ainsi que des produits auxiliaires de formulation.
  3. Procédé de préparation d'un composé de formule générale I' selon la revendication 1.    dans laquelle
       R1 et R2 ont la signification donnée dans la revendication 1,
       caractérisé en ce que l'on fait réagir un composé de formule générale    dans laquelle R1 et R2 ont la signification donnée dans la revendication 1,
       avec un dérivé de l'alcool benzylique de formule générale    dans laquelle
       U représente un groupe éliminable.
  4. Procédé pour combattre les mycètes dans l'agriculture et l'horticulture, caractérisé en ce que l'on traite l'objet à protéger par une quantité efficace d'un composé selon la revendication 1 ou d'un produit selon la revendication 2.
  5. Utilisation d'un composé selon la revendication 1 ou d'un produit selon la revendication 2 pour la lutte contre les mycètes dans l'agriculture et l'horticulture.
EP89913190A 1988-12-29 1989-12-12 Esters methyliques aldimino- ou cetimino-oxy-ortho-tolylacryliques, mode de fabrication et fongicides contenant a ces composes Expired - Lifetime EP0403618B2 (fr)

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CH397589 1989-11-03
PCT/CH1989/000216 WO1990007493A1 (fr) 1988-12-29 1989-12-12 Esters methyliques aldimino- ou cetimino-oxy-ortho-tolylacryliques, mode de fabrication et fongicides contenant a ces composes

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EP0370629B2 (fr) * 1988-11-21 1998-01-07 Zeneca Limited Fongicides
US5104872A (en) * 1989-08-22 1992-04-14 Nihon Hohyaku Co., Ltd. N-(substituted benzyloxy) imine derivatives and method of use thereof
DE59108900D1 (de) * 1990-06-27 1998-01-22 Basf Ag O-Benzyl-Oximether und diese Verbindungen enthaltende Pflanzenschutzmittel
GB9018408D0 (en) * 1990-08-22 1990-10-03 Ici Plc Fungicides
EP0569384B2 (fr) * 1991-01-30 2000-10-04 Zeneca Limited Fongicides
NZ242290A (en) * 1991-04-15 1994-12-22 Zeneca Ltd Pyridyl and pyrimidinyl substituted oxime-o-benzyl ether derivatives; preparatory processes, fungicidal compositions and an intermediate
CH686307A5 (de) * 1991-04-19 1996-02-29 Ciba Geigy Ag Oximether des 3-Methoxy-2-(o-tolyl)acrylsouremethylesters, Verfahren zu ihrer Herstellung und fungizide Mittel, die diese als Wirkstoffe enthalten.
EP0621864B1 (fr) * 1991-10-25 1996-12-27 Ciba-Geigy Ag DERIVES DE -2-IMINOACETATE-3-METHOXYACRYLATE ET 2-(2-BENZO(b)THIENYLE), UTILISES COMME PESTICIDES
TW221965B (fr) * 1992-02-28 1994-04-01 Ciba Geigy
GB9221584D0 (en) * 1992-10-14 1992-11-25 Ici Plc Chemical process
GB9221526D0 (en) * 1992-10-14 1992-11-25 Ici Plc Fungicides
GB9226865D0 (en) * 1992-12-23 1993-02-17 Ici Plc Fungicides
IT1263751B (it) * 1993-02-05 1996-08-27 Mini Ricerca Scient Tecnolog Derivati di esteri arilacetici ad attivita' fungicida
AU690190B2 (en) * 1994-01-05 1998-04-23 Bayer Aktiengesellschaft Pesticides
US5889059A (en) * 1994-02-04 1999-03-30 Basf Aktiengesellschaft Phenylacetic acid derivatives, preparation thereof and intermediates therefor, and compositions containing them
AU686304B2 (en) * 1994-02-04 1998-02-05 Basf Aktiengesellschaft Phenylthio acetic acid derivatives, process and intermediateproducts for their production and agents containing them
CZ293803B6 (cs) * 1994-02-04 2004-08-18 Basfáaktiengesellschaft Deriváty fenyloctové kyselinyŹ způsob jejich přípravyŹ prostředekŹ způsob potírání zvířecích škůdců nebo škodlivých hub
GB9405492D0 (en) * 1994-03-21 1994-05-04 Zeneca Ltd Chemical compounds
US5583249A (en) * 1994-08-19 1996-12-10 Ciba-Geigy Corporation Pesticides
CH689228A5 (de) * 1994-10-07 1998-12-31 Novartis Ag Oximether, sowie diese enthaltende Pflanzenschutzmittel.
ATE187960T1 (de) * 1994-11-17 2000-01-15 Novartis Erfind Verwalt Gmbh Derivate von o-benzyl-oxin-ether sowie deren verwendung als pestizide
JPH08176146A (ja) * 1994-12-19 1996-07-09 Idemitsu Kosan Co Ltd ピラゾール誘導体の製造法
UA54395C2 (uk) * 1995-06-16 2003-03-17 Баєр Акціенгезельшафт Фітобактерициднa композиція, спосіб контролю та запобігання хворобам рослин, матеріал для розмноження рослин
MY115814A (en) * 1995-06-16 2003-09-30 Bayer Ip Gmbh Crop protection compositions
ES2146888T3 (es) 1995-06-27 2000-08-16 Novartis Ag Derivados de eter de o-benziloxima y su uso en composiciones para la proteccion de cultivos.
DE19523288A1 (de) * 1995-06-27 1997-01-02 Basf Ag Iminooxybenzylverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung
CZ423897A3 (cs) * 1995-07-04 1998-04-15 Novartis Ag Bis-oximderiváty triazolinu a isoxazolinu, způsob jejich přípravy a meziprodukty v tomto způsobu, pesticidní prostředky, které je obsahují, a jejich použití
GB9516788D0 (en) * 1995-08-16 1995-10-18 Agrevo Uk Ltd Fungicides
DE19539324A1 (de) * 1995-10-23 1997-04-24 Basf Ag Phenylessigsäurederivate, Verfahren und Zwischenprodukte zu ihrer Herstellung und sie enthaltende Mittel
US5739140A (en) * 1995-11-03 1998-04-14 Monsanto Company Selected novel aryl acrylics
AU717468B2 (en) 1995-12-07 2000-03-30 Bayer Aktiengesellschaft Process for the preparation of pesticides
PL185913B1 (pl) 1995-12-07 2003-08-29 Bayer Ag Pochodne strobiluryny, sposób wytwarzania pochodnyPochodne strobiluryny, sposób wytwarzania pochodnych strobiluryny, związki pośrednie, sposób wytwarzch strobiluryny, związki pośrednie, sposób wytwarzania związków pośrednich, kompozycja pestycydowa oania związków pośrednich, kompozycja pestycydowa oraz zastosowanie pochodnych strobilurynyraz zastosowanie pochodnych strobiluryny
AU1546197A (en) 1996-02-05 1997-08-28 Basf Aktiengesellschaft Pyrimidine derivatives, process and intermediate products for their preparation and pesticides or fungicides containing these derivatives
AU2696697A (en) * 1996-04-26 1997-11-19 Novartis Ag Pesticidal compositions
US6084120A (en) * 1997-07-09 2000-07-04 Hoffmann-La Roche Inc. β-Alkoxyacrylates against malaria
CN1062711C (zh) * 1998-02-10 2001-03-07 化工部沈阳化工研究院 不饱和肟醚类杀虫、杀真菌剂
DE69906170T2 (de) * 1998-02-10 2003-10-23 Dow Agrosciences Llc Ungesättigte Oxim-Ether und ihre Verwendung als Fungizide oder Insectizide
FR2777003A1 (fr) * 1998-04-07 1999-10-01 Rhone Poulenc Agrochimie Nouveaux composes fongicides
FR2777002A1 (fr) * 1998-04-07 1999-10-08 Rhone Poulenc Agrochimie Nouveaux composes fongicides
US6313344B1 (en) 1998-05-27 2001-11-06 Bayer Aktiengesellschaft Organic compounds
AU1007400A (en) * 1999-01-27 2000-08-03 Dow Agrosciences Llc Aryl and heteroarylcyclopropyl oxime ethers and their use as fungicides and insecticides
SK5992002A3 (en) * 1999-11-05 2003-02-04 Nippon Soda Co Oxime O-ether compounds and fungicides for agricultural and horticultural use
EP1125931A1 (fr) * 2000-02-17 2001-08-22 Hunan Research Institute of Chemical Industry (Hétéro)aryl-kétoxime-O-éthers alkyle substitués et méthode pour les fabriquer
CN1179942C (zh) * 2002-09-13 2004-12-15 湖南化工研究院 具有杀菌活性的含硫不饱和肟醚类化合物及其制备方法
US20050215626A1 (en) * 2003-09-25 2005-09-29 Wyeth Substituted benzofuran oximes
WO2007039555A1 (fr) * 2005-10-06 2007-04-12 Basf Aktiengesellschaft Composés de type éther-oxime et leur utilisation comme pesticides
CN103601716A (zh) * 2013-11-20 2014-02-26 厦门大学 一种苯并噻吩取代肟醚类化合物及其制备方法与应用
CN103980179A (zh) * 2014-05-29 2014-08-13 厦门大学 一种吲哚取代肟醚类化合物及其制备方法与应用
WO2016193267A1 (fr) * 2015-06-02 2016-12-08 Syngenta Participations Ag Compositions de lutte contre les moustiques vecteurs, méthodes et produits l'utilisant
CN106995417B (zh) 2016-01-26 2019-05-31 南开大学 一类异噻唑肟醚甲氧基丙烯酸酯衍生物及其制备方法和用途
WO2017129122A1 (fr) * 2016-01-26 2017-08-03 南开大学 Dérivés de strobilurine d'étheroxime d'isothiazole, leur procédé de préparation et leurs utilisations
WO2017129121A1 (fr) * 2016-01-26 2017-08-03 南开大学 Dérivés de strobilurine d'étheroxime de thiadiazole, leur procédé de préparation et leur utilisation
RU2698300C1 (ru) * 2018-07-04 2019-08-26 Федеральное государственное бюджетное образовательное учреждение высшего образования "Российский химико-технологический университет имени Д.И. Менделеева" (РХТУ им. Д.И. Менделеева) Замещенные метил-n-метоксикарбаматы
AR115870A1 (es) 2018-07-31 2021-03-10 Sumitomo Chemical Co MÉTODO PARA CONTROLAR EL HONGO DE LA ROYA DE LA SOJA QUE TIENE RESISTENCIA AL INHIBIDOR DE SITIO Qₒ
JP2023022345A (ja) * 2020-01-31 2023-02-15 住友化学株式会社 植物病害防除組成物及び植物病害防除方法
US20230255200A1 (en) 2020-07-08 2023-08-17 Basf Se Use of strobilurin type compounds for combating phytopathogenic fungi containing an amino acid substitution f129l in the mitochondrial cytochrome b protein conferring resistance to qo inhibitors vi
CN113582970B (zh) * 2021-07-02 2023-07-14 凯里学院 含酰胺及肟或肟醚结构的硫色满-4-酮衍生物的制备方法及应用
CN113956247B (zh) * 2021-10-27 2023-07-11 凯里学院 含1,3,4-噁二唑硫醚及肟醚结构的硫色满-4-酮衍生物的制备方法及应用

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2025407B (en) * 1978-07-03 1982-10-27 Shell Int Research Benzyloxime ethers and their use as pesticides

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NO173543B (no) 1993-09-20
JPH03503056A (ja) 1991-07-11
EP0403618A1 (fr) 1990-12-27
AU4639089A (en) 1990-08-01
ATE117983T1 (de) 1995-02-15
NO903771D0 (no) 1990-08-28
PT92753A (pt) 1990-06-29
DK206290A (da) 1990-08-28
DE58908972D1 (de) 1995-03-16
NO173543C (no) 1993-12-29
MX9202638A (es) 1992-06-30
WO1990007493A1 (fr) 1990-07-12
EP0403618B1 (fr) 1995-02-01
HU900284D0 (en) 1991-05-28
ES2067570T3 (es) 1995-04-01
KR100187541B1 (ko) 1999-06-01
HU216144B (hu) 1999-04-28
BR8907287A (pt) 1991-03-12
HUT55951A (en) 1991-07-29
NO903771L (no) 1990-08-28
NZ231891A (en) 1992-08-26
CA2005345A1 (fr) 1990-06-29
KR910700228A (ko) 1991-03-14
JP2907540B2 (ja) 1999-06-21
FI904230A0 (fi) 1990-08-27
PT92753B (pt) 1995-12-29

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